US1751318A - Process for obtaining photographic images - Google Patents
Process for obtaining photographic images Download PDFInfo
- Publication number
- US1751318A US1751318A US141671A US14167126A US1751318A US 1751318 A US1751318 A US 1751318A US 141671 A US141671 A US 141671A US 14167126 A US14167126 A US 14167126A US 1751318 A US1751318 A US 1751318A
- Authority
- US
- United States
- Prior art keywords
- photographic images
- phenols
- obtaining photographic
- obtaining
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- -1 di and tri-phenols Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 150000002790 naphthalenes Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
Definitions
- the invention consists in adding to the diazo bodies forming the sensitive film or layer certain substances which produce phenols or naphthols by the action of alkalies, which permits sensitive films or layers to be obtained which can be developed by the simple action of alkaline substances (vapours of ammonia or alkaline baths).
- the difliculty referred to is obviated in replacing phenol or naphthol by one of its acetyl derivatives capable of regeneration under the action of the alkali employed during 'the development, which is introduced only at the moment of development.
- Theacetyl derivatives of phenols, di and tri-phenols, naphthols, dioxynaphthalines and amidonaphthols lend themselves particularly well to obtaining stable mixtures With diazo bodies in a neutral medium.
- Ac. (in which R represents a benzene or naphthalene nucleus substituted or not substituted and Ac. denotes an acid radicle) may be employed. Certain of these products being slightly soluble in water their sulpho or carboxyl derivatives may be used or even the alkaline salts of these derivatives.
- the diazo body and the acetyl derivative of phenol or naphthol are mixed and the mixture used for the formation of the sensitive film or layer on the support, so that on exposure to light under a drawing or the like, the imagefin azo colour,
- the colour which constitutes the image is identical with that obtained by coupling of the diazohydroquinonedimethyl ether and the chromotropic acid, that is to say, that it has the property of giving lakes with metallic salts, which permits of varying the shade by trial either in toning them in baths of metallic salts after development .or in introducing these salts in the sensitive bath.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
Description
Patented Mar. 18, 1930 UNITED STATES;
PATENT OFFICE EUGENE GAY, or LYON, rRANoE N Drawing. Application filed October 14, 1926, Serial No. 141,671, and in France October 23, 1925.
In the specification filed upon a co-pending application Serial No. 141,670, dated 14th October, 1926, a process is described for obtaining photographic images based upon the formation of azo dyes by reaction of diazo bodies sensitive to the action of light upon phenols or amines in the presence of alkali.
The invention consists in adding to the diazo bodies forming the sensitive film or layer certain substances which produce phenols or naphthols by the action of alkalies, which permits sensitive films or layers to be obtained which can be developed by the simple action of alkaline substances (vapours of ammonia or alkaline baths).
It has been established that the speed of reaction of diazo bodies with phenols which is high in an alkaline medium is often far from negligible in a neutral medium and this constitutes an obstacle to the use of mixtures of diazo bodies with phenols for obtaining sensitive films or layers suitable for developing by the simple action of alkalies.
This disadvantage can be remedied up to a certainpoint by acidifying the mixture. Thus the speed of the reaction is diminished but this effect is secured to the detriment of the preservation of the substance of the support such as paper that is employed. In fact this leads with certain diazo bodies and certain phenols to the use of an inadmissable quantity of acid. 1 i
The difliculty referred to is obviated in replacing phenol or naphthol by one of its acetyl derivatives capable of regeneration under the action of the alkali employed during 'the development, which is introduced only at the moment of development.
40 Theacetyl derivatives of phenols, di and tri-phenols, naphthols, dioxynaphthalines and amidonaphthols lend themselves particularly well to obtaining stable mixtures With diazo bodies in a neutral medium. The phenolic estersderived from formic acid, oxalic acid or benzene-sulphonic acid and generally the aromatic bodies R. 0. Ac. (in which R represents a benzene or naphthalene nucleus substituted or not substituted and Ac. denotes an acid radicle) may be employed. Certain of these products being slightly soluble in water their sulpho or carboxyl derivatives may be used or even the alkaline salts of these derivatives. The diazo body and the acetyl derivative of phenol or naphthol are mixed and the mixture used for the formation of the sensitive film or layer on the support, so that on exposure to light under a drawing or the like, the imagefin azo colour,
is produced by development of the exposed film or layer by means of an alkali only.
Thus, tor example, there is added to one litre of a bath of the diazohydroquinonedimethyl ether obtained according to'the directions given in the specification filed upon the said co-pending application, 30 gr. of 1-8-diacetyldioXynaphthalene-3-G-disulphonic acid and one litre of water.
A sheet of paper or-other convenient support impregnated in this bath, dried and exposed to light under a transparent design, until the parts not protected by the'design are decoloured, yields by development with the ammonia vapour a positive violet red image. The colour which constitutes the image is identical with that obtained by coupling of the diazohydroquinonedimethyl ether and the chromotropic acid, that is to say, that it has the property of giving lakes with metallic salts, which permits of varying the shade by trial either in toning them in baths of metallic salts after development .or in introducing these salts in the sensitive bath.
I claim:
A process for obtaining. a photographic ii'nage of the kind described, consisting in impregnating a substance having a surface adapted for the reception of a photographic image in a bath of I-S-diacetyldioxynaphthalene-3-6-disulphonic acid and diazohydroquinonedimethyl ether, drying the said substance and exposing the substance under a transparent design having substantially opaque parts and developing by an alkali to yield a positive violet red image, substantially as hereinbefore described.
EUGENE GAY.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR616562T | 1925-10-20 | ||
| FR31582T | 1925-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1751318A true US1751318A (en) | 1930-03-18 |
Family
ID=26235328
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US141671A Expired - Lifetime US1751318A (en) | 1925-10-20 | 1926-10-14 | Process for obtaining photographic images |
| US141670A Expired - Lifetime US1841801A (en) | 1925-10-20 | 1926-10-14 | Process for obtaining photographic images |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US141670A Expired - Lifetime US1841801A (en) | 1925-10-20 | 1926-10-14 | Process for obtaining photographic images |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US1751318A (en) |
| BE (2) | BE336886A (en) |
| DE (1) | DE545486C (en) |
| FR (2) | FR616562A (en) |
| GB (2) | GB282894A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2416021A (en) * | 1944-12-29 | 1947-02-18 | Gen Aniline & Film Corp | Light sensitive diazotype compositions and process |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE763721C (en) * | 1942-02-19 | 1953-10-05 | Kalle & Co Ag | Photosensitive layers |
| BE473113A (en) * | 1946-05-08 | |||
| FR1055783A (en) * | 1950-03-28 | 1954-02-22 | Equipment and method for obtaining photographic images on textiles and flexible materials | |
| US5451566A (en) * | 1993-11-17 | 1995-09-19 | Zeneca Limited | Herbicidal pyrrolopyridine compounds |
| US10600748B2 (en) | 2016-06-20 | 2020-03-24 | Samsung Electronics Co., Ltd. | Fan-out semiconductor package |
-
0
- BE BE336885D patent/BE336885A/xx unknown
- BE BE336886D patent/BE336886A/xx unknown
-
1925
- 1925-10-20 FR FR616562D patent/FR616562A/en not_active Expired
- 1925-10-23 FR FR31582D patent/FR31582E/en not_active Expired
-
1926
- 1926-03-21 DE DEG66897D patent/DE545486C/en not_active Expired
- 1926-09-30 GB GB24191/26A patent/GB282894A/en not_active Expired
- 1926-10-06 GB GB24844/26A patent/GB283274A/en not_active Expired
- 1926-10-14 US US141671A patent/US1751318A/en not_active Expired - Lifetime
- 1926-10-14 US US141670A patent/US1841801A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2416021A (en) * | 1944-12-29 | 1947-02-18 | Gen Aniline & Film Corp | Light sensitive diazotype compositions and process |
Also Published As
| Publication number | Publication date |
|---|---|
| DE545486C (en) | 1932-03-01 |
| BE336885A (en) | |
| FR31582E (en) | 1927-03-17 |
| BE336886A (en) | |
| US1841801A (en) | 1932-01-19 |
| GB282894A (en) | 1927-12-30 |
| FR616562A (en) | 1927-02-04 |
| GB283274A (en) | 1928-01-06 |
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